Drinking With The Enemy
by VonHosselfratt
Summary: Karen Walker and Will Truman may not be the best of friends. But they make for surprisingly compatible drinking buddies.


**A/N This one-shot is set after the Finale and is inspired by the friendship(?) between Will Truman and Karen Walker. Hope you like it and don't forget to review!**

* * *

"Sorry I'm late, Wilma."

Karen appears beside Will, dropping her clutch purse unceremoniously on the bar stool and hoisting herself up on the adjacent one in a single motion. She's dressed immaculately in a figure-hugging suit and sleek Louboutins, despite her (admittedly enigmatic) age, looking as radiant as ever.

Will glances across at her, doing his best to give her a condescending glower despite a mouth full of peanuts. He swallows them with an audible gulp and wipes his mouth irritably.

"Karen," he says stiffly, "I'm not your _poodle_ , okay? I'm your lawyer. If you set a date for eight o'clock I expect you to be here at…" He sighs. "Well, definitely not _on time_ but less than ninety minutes late!" He tilts his head angrily. "I've been stuck here ordering mediocre bar food for the past hour and a half."

Karen cackles to herself.

"Okay, first off, don't flatter yourself. You're not a poodle. These days you're more…" she wrinkles her nose in distaste and gestures with her fingers, "like one of those diseased St Bernard dogs at the pound that got rejected during mating season and then crept off to eat everyone else's kibble. Smitty _, a gin, please_. And second, this isn't a business meeting, Wilma. Jack's out of town visiting his son in college - _did you know he has a son, by the way?_ \- And I need a drinking buddy."

She grabs her gin and downs half of it in one gulp. Will's expression softens.

"You wanted to drink? With me? Even though the last time we drank together, we both ended up uncovering emotional scars that will probably never heal?"

"Sure, honey," Karen smiles. "I've always felt that you were the yin to my yang."

"Really?" Will is touched.

"Yeah, in the sense that I'm a hot firecracker with a killer body and you're…" she frowns. "A lawyer with a boring personality and a wardrobe that ranges from _gray suit_ to _brown suit_."

"Ah."

"What's up with that, by the way? That ensemble is a disgrace to your entire community," she says, gesturing at Will's attire.

He shifts uncomfortably.

"Well, you'll have to forgive me. I _assumed_ I was here in a purely business capacity. I guess I can…" He begins to loosen his collar a little.

Karen rolls her eyes.

"Oh, _lord_. Come here, Wilma." She reaches across to unfasten the top two buttons of his shirt, then ruffles his hair until it's tousled.

"Karen!" Will protests weakly as she steps back to view her handiwork.

"Better," she says. "You look less like a repressed Mormon missionary and more like an actual drinking partner." She raises her glass. "Now you just need an alias. Something cute and spunky. Like...Billy the Kid."

"And what are you, Butch Cassidy?" Will says, deadpan.

"That's Anastasia Beaverhausen to you, kid," Karen drawls in reply. "Now, Smitty, get Billy boy here a Blue Marilyn."

Will sits up, startled.

"They serve Blue Marilyns here?"

"They do now. Your mommy may have her issues, but she makes one hell of a libation."

Will idly reaches for the peanuts, and Karen promptly smacks them out his hand.

"Hey!" He pouts.

"Hey, fatty. You've guzzled enough empty calories tonight. Tonight we're getting drunk."

"Are you implying that you're currently sober?" Will snarks.

"Yes, and it's _exhausting_."

Will eyes the Blue Marilyn suspiciously as it's placed in front of him.

"...You know I've seen my mom down at least twelve of these on every special occasion since childhood - and by special occasion, I mean days that end in 'Y'..." he frowns. "But I've never actually had one myself."

"Try it. Knowing your genetics, it can't be that much of a shock to your system. I know there's a hardened alcoholic hiding somewhere in that DNA of yours."

Will sips it tentatively, and swallows.

He screws up his face.

"That's intense," he says. "I can't drink this whole thing. I'll be drunk in two minutes."

"Why are you so scared to let loose a little?" Karen nags. "Are you scared that if you get a little tipsy, you might find yourself a little attracted to _Ms Karen Delaney-Walker-More-Names-That-I-Don't-Remember_?"

"Oh please," Will scoffs. "In order to be attracted to you, I'd need to be ninety-five percent less gay and a thousand percent more drunk. I mean, it would take a _lot_ of Blue Marilyns."

"The night is young, Wilma," Karen purrs, mock-flirtatiously, sliding the drink towards him with one idle finger.

Will purses his lips.

"I mean, I suppose I could be attracted to you in theory. If you didn't speak, and I squinted a little, I could almost mistake you for a drag queen."

"Hey, politically incorrect humor is only funny when I do it. When you do it, it's just sad," Karen informs him matter-of-factly. "Smitty, a tequila, please."

"And I guess there would be something quite quaint about making love to something that's older than the Aztec Empire," Will muses, taking another sip of his drink. It's still strong, but tangy in way that leaves a pleasant buzz in his stomach.

"It's so cute when you make those age jokes. Need I remind you that I'm only a few years your senior."

Will exhales in amusement. "A few centuries, more like."

"That's rich. I'm not the one with gray hair."

Will ducks his head, startled, and grabs at his hair protectively.

"What? I am _not_ gray," he hisses. "I mean, sometimes a little, but I dye the tips!"

"Relax, I just wanted to see how you'd react," Karen cackles. "Boy, was it entertaining. I'll never know why _Aging Queens of Upper West Side_ didn't take off at OutTV."

"Oh, and its spinoff series, _The Socialite Hags Who Abuse Them_?" Will snaps.

"Once again, Wilma, that kind of humor just doesn't work well with you as it does with me." Karen smiles sweetly. "Now drink up."

* * *

"Okay, okay, okay, okay," Will slurs, leaning forward on the bar on his elbows. "Explain this game to me again."

"You have to screw one, marry one, and waste the other," Karen says. "So we've got Grace, Jack and me. Choose wisely."

"I mean obviously I'm going to kill you, no questions asked," Will says, grinning widely at the thought. "And I guess I'd marry Grace...but she's in Rome with _Leo_." He spits out the last word and lets his head droop, suddenly somber.

"Hey, should I be offended that you're only questioning the hypothetical nature of the game _after_ killing me?" Karen says, feigning shock.

"Aw, Kare," Will murmurs "You know it's nothing personal. I mean, it's just - at your age, with your liver...it's only a matter of time." He reaches across clumsily and pats her on the head.

"I'd sleep with one eye open if I were you," she says darkly, but there's a playful gleam in her eye. "I guess that means you're screwing Jack."

Will scoffs, then laughs, nodding.

" _Sure_ , okay. I mean, he's Jack, but he gets points for...you know...actually having a penis."

"Really, _that's_ your requirement?" Karen says. "I have one of _those_."

"What?"

"What?"

"Huh?"

"Moving on," Karen says. "Why don't you take this and go play a little something on the jukebox?" She slams a hundred dollar bill on the bar.

"...Karen, I know that your lavish lifestyle must have given you a really twisted sense of currency," Will says slowly. "But a song only costs a _quarter_."

"What's a quarter?" Karen asks innocently.

Will throws her an incredulous look.

"...I don't even know if you're joking at this point."

Karen stares blankly, then pats him on the cheek.

"Be a good poodle and go put on some music. Mama wants to dance."

Will begins to protest the nickname, but then realizes that coming from Karen, it's a compliment.

He smiles.

* * *

 _It's Not Unusual_ is blasting from the jukebox.

Will and Karen are dancing wildly, offbeat and singing - or rather yelling - slurred lyrics to each other.

"Don't you think this _is_ a little unusual?" Will yells, louder than really necessary. "You know, you and me; hanging out?"

"No, honey," Karen smiles, still bopping to the beat. "If you think about it, you and I have always been the solid foundation of our friendship group."

Will snorts. "Oh really?"

"Sure. I mean, Jack changes occupation every Wednesday - always running off with a new _Don Juan_ , or _Juan Don_ , or _Kevin Bacon_...and Grace, bless her soul, was always so flighty - giving out her office keys to random guys including married men and greeting card writers who pen screenplays about euthanasia..." Karen sighs. "But you and me, we were always so unchanging. People could always rely on me to be rich, stylish and hilarious. And you...well you were always just…Will." She smiles. "Boring, uptight, irritable Will."

"Aw, thanks Kare," Will smiles, wrapping his arms around her and swaying with her gently, despite the fast pace of the music. "That means a lot to me. And trust me, if I was straight…"

Karen raises one eyebrow suggestively. "If you were straight?"

Will laughs in response, then slams a hand over his mouth.

"Oh god. I got a little bile in my throat just thinking about it."

Karen scowls, and bats him on the shoulder.

* * *

"Remember that time we kissed?" Karen says, smiling tenderly.

"Sure, you made out with me after I read out the speech I wrote for Jack's graduation," Will murmurs, thoughtfully running a languid finger around the rim of his glass. "I have to say it's the best critical response I've ever gotten from my short-lived stint in writing."

"Actually," she says, "I'm talking about that time you dipped me at that dancing event."

"Ah yes," Will says tenderly. "And then I kissed you in front of Beverly Leslie and all those women who thought I was a whore."

"My whore," Karen cuts in.

"I have to admit, for a moment there we did have some pretty raw sexual chemistry," Will says.

"Oh, please. I have raw sexual chemistry with everybody," she replies, flipping her hair a little.

Will giggles, then groans.

"Oh god. I've had way too much to drink."

"If you want, you can sleep in my limo," Karen offers. "Just don't be surprised if Rosario gets little handsy. She always gets horny around Cinco De Mayo."

"Nah, I'll be fine," Will says, his voice straining as he stands up. "Vince is expecting me home by ten anyway."

"Honey, it's twelve past midnight."

"Oh god, really? Please tell me that's a joke!" Will grabs his cell phone and flips it open, panicking.

"No, sweetie, what's a joke is that it's 2008 and you still own a clamshell phone. Remind me to get you an upgrade," Karen retorts nonchalantly.

Will dials clumsily and holds the phone to his ear, grimacing.

"Hey Vince? Look, _so_ sorry I'm late home, I ...yeah, I know, _I'm sorry, I'm sorry,_ I...Well, I know Ben wanted me to read him _The Very Hungry Caterpillar_ , but I can do it tomorrow night...yes, I _know_ it was my turn...I'll make it up to you, I promise. Look, I'm on my way home right now...Love you too."

Will hangs up, sighing.

"Remind me to never get drunk with you again," he snaps, stuffing his phone angrily back into his pocket.

Karen pouts.

"But we were having so much fun!" she whines. "And with Grace and Jack gone, I just...thought it would be nice to get what was left of the gang back together. Even if the gang was just... _you_."

Will smiles softly and braces his hands on Karen's shoulders.

"I know what you mean," he says. "But - 'the gang' as you call it - will always be together in spirit. We're just...all focused on family right now. A new chapter in our lives. That doesn't mean that we can't go back and...revisit those old chapters every now and then." He exhales wistfully. "Just maybe...not so often as we used to."

Karen returns the smile.

"And if you think about it," he continues wryly. "I owe a lot of it to you. I mean, if it wasn't for you and your terrible driving skills, I never would have met the love of my life. I might not even have Ben."

" _Lord_ , we're getting sentimental again," Karen says in annoyance.

"It's almost like you're my fairy godmother," Will continues airily.

"Who are you calling fairy, fairy?!" she snaps, poking him squarely in the chest. He staggers backwards, laughing. "Call me your mother again and I'll make your death look like a hilarious accident."

"Love you too, Karen," he smiles. "Well, I'd better get back home."

"Call me?" she says hopefully.

He walks backwards towards the entrance and gives her a lazy, drunken grin.

"I'll call you," he promises.

He shakes his head as he leaves the bar. She may not be Grace, but she'll do for now.

Karen watches him leave, and sighs before ordering another drink.

He may not be Jack, but he'll do for now.

* * *

 **A/N I've always been intrigued by the enigmatic relationship between Will and Karen. There's hatred, sure, but there's a certain respect and understanding between them that I've always loved. This one-shot was my little way of expressing my love for them.**

 **This is my first time writing Karen Walker so forgive me if it wasn't great. Reviews would be awesome.**


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